|Preferred IUPAC name
3D model (JSmol)
|Molar mass||57.051 g/mol|
|Odor||Sharp, pungent odor|
|Density||0.9230 g/cm3 at 27 °C|
|Melting point||−45 °C (−49 °F; 228 K) |
|Boiling point||38.3 °C (100.9 °F; 311.4 K) |
|Vapor pressure||57.7 kPa|
Std enthalpy of
|R-phrases (outdated)||R12, R24/25, R26, R37/38, R41, R42/43, R63|
|S-phrases (outdated)||(S1/2), S26, S27/28, S36/37/39, S45, S63|
|Flash point||−7 °C (19 °F; 266 K)|
|534 °C (993 °F; 807 K)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|120 mg/kg (oral, mouse)|
51.5 mg/kg (oral, rat)
LC50 (median concentration)
|6.1 ppm (rat, 6 hr)|
12.2 ppm (mouse, 6 hr)
5.4 ppm (guinea pig, 6 hr)
21 ppm (rat, 2 hr)
|US health exposure limits (NIOSH):|
|TWA 0.02 ppm (0.05 mg/m3) [skin]|
|TWA 0.02 ppm (0.05 mg/m3) [skin]|
IDLH (Immediate danger)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Methyl isocyanate (MIC) is an organic compound with the molecular formula CH3NCO. Synonyms are isocyanatomethane, methyl carbylamine and MIC. Methyl isocyanate is an intermediate chemical in the production of carbamate pesticides (such as carbaryl, carbofuran, methomyl, and aldicarb). It has also been used in the production of rubbers and adhesives. As a highly toxic and irritating material, it is extremely hazardous to human health. It was the principal toxicant involved in the Bhopal disaster, which killed 3,787 people initially and officially 19,787 people in total.
Methyl isocyanate is a colorless, poisonous, lachrymatory (tearing agent), flammable liquid. It is soluble in water to 6–10 parts per 100 parts, but it also reacts with water (see Reactions below).
Methyl isocyanate is usually manufactured by the reaction of monomethylamine and phosgene. For large scale production, it is advantageous to combine these reactants at higher temperature in the gas phase. A mixture of methyl isocyanate and two moles of hydrogen chloride is formed, but N-methylcarbamoyl chloride (MCC) forms as the mixture is condensed, leaving one mole of hydrogen chloride as a gas.
Methyl isocyanate is also manufactured from N-methylformamide and air. In the latter process, it is immediately consumed in a closed-loop process to make methomyl. Other manufacturing methods have been reported.
Methyl isocyanate reacts readily with many substances that contain N-H or O-H groups. With water, it forms 1,3-dimethylurea and carbon dioxide with the evolution of heat (325 calories per gram of MIC):
At 25 °C, in excess water, half of the MIC is consumed in 9 min.; if the heat is not efficiently removed from the mixture, the rate of the reaction will increase and rapidly cause the MIC to boil. If MIC is in excess, 1,3,5-trimethylbiuret is formed along with carbon dioxide. Alcohols and phenols, which contain an O-H group, react slowly with MIC, but the reaction can be catalyzed by trialkylamines or dialkyltin dicarboxylate. Oximes, hydroxylamines, and enols also react with MIC to form methylcarbamates. These reactions produce the products described below (Uses).
It also reacts with itself to form a trimer or higher molecular weight polymers. In the presence of catalysts, MIC reacts with itself to form a solid trimer, trimethyl isocyanurate, or a higher molecular weight polymer:
Sodium methoxide, triethyl phosphine, ferric chloride and certain other metal compounds catalyze the formation of the MIC-trimer, while the high-molecular-weight polymer formation is catalyzed by certain trialkylamines. Since the formation of the MIC trimer is exothermic (298 calories per gram of MIC), the reaction can lead to violent boiling of the MIC. The high-molecular-weight polymer hydrolyzes in hot water to form the trimethyl isocyanurate. Since catalytic metal salts can be formed from impurities in commercial grade MIC and steel, this product must not be stored in steel drums or tanks.
Methyl isocyanate is extremely toxic. The threshold limit value set by the American Conference on Government Industrial Hygienists is 0.02 ppm. MIC is toxic by inhalation, ingestion and contact in quantities as low as 0.4 ppm. Exposure symptoms include coughing, chest pain, dyspnea, asthma, irritation of the eyes, nose and throat, as well as skin damage. Higher levels of exposure, over 21 ppm, can result in pulmonary or lung edema, emphysema and hemorrhages, bronchial pneumonia and death. Although the odor of methyl isocyanate cannot be detected at 5 ppm by most people, its potent lachrymal properties provide an excellent warning of its presence (at a concentration of 2–4 parts per million (ppm) subject's eyes are irritated, while at 21 ppm, subjects could not tolerate the presence of methyl isocyanate in air).
Proper care must be taken to store methyl isocyanate because of its ease of exothermically polymerizing (see Reactions) and its similar sensitivity to water. Only stainless steel or glass containers may be safely used; the MIC must be stored at temperatures below 40 °C (104 °F) and preferably at 4 °C (39 °F).
The toxic effect of the compound was apparent in the 1984 Bhopal disaster, when around 42,000 kilograms (93,000 lb) of methyl isocyanate and other gases were released from the underground reservoirs of the Union Carbide India Limited (UCIL) factory, over a populated area on December 3, 1984, killing about 3,500 people immediately and 15,000 more over the next several years.
On 30 July 2015, scientists reported that upon the first touchdown of the Philae lander on comet 67/P's surface, measurements by the COSAC and Ptolemy instruments revealed sixteen organic compounds, four of which were seen for the first time on a comet, including acetamide, acetone, methyl isocyanate and propionaldehyde.
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- ‹See Tfd›US patent 2480088, ‹See Tfd›Slocombe, R. J.; Hardy, E. E., "Process of Producing Carbamyl Chlorides", issued 1949-08-23, assigned to Monsanto
- ‹See Tfd›FR patent 1400863, ‹See Tfd›Merz, W., "Procédé et dispositif de préparation d'isocyanates d'alkyle", issued 1965-05-28, assigned to Bayer
- Chemical Week, "A fleeting existence for toxic-gas molecules" p. 9, June 12, 1985.
- ‹See Tfd›DE patent 2828259, ‹See Tfd›Giesselmann, G.; Guenther, K.; Fuenten, W., "Verfahren zur Herstellung von Methyl Isocyanate", issued 1980-01-10, assigned to Degussa
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- "Bhopal trial: Eight convicted over India gas disaster". BBC News. 7 June 2010. Archived from the original on 7 June 2010. Retrieved 7 June 2010.
- "ALMA Finds Ingredient of Life Around Infant Sun-like Stars". www.eso.org. Archived from the original on 8 June 2017. Retrieved 8 June 2017.
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- NIOSH Safety and Health Topic: Isocyanates, from the website of the National Institute for Occupational Safety and Health (NIOSH).
- U.S. National Library of Medicine: Hazardous Substances Databank – Methyl isocyanate